Dating on vacation: Dead end, escape from routine or a little of both?

“Lisa, you should go to Santorini with a boyfriend,” one of my Greek relatives said while hosting me in the Athens suburbs for a few days before I left for a week in the islands.

“She will meet a Greek boyfriend!” her husband countered. “Or an American one.”

It wasn’t my safety as a solo traveler that my hosts seemed to be concerned with, but my heart. I interpreted their question as: How could you go to one of the world’s most romantic spots on your own?

Perhaps. But I’d always wanted to visit the Greek islands, and I was done waiting. Santorini was on the top of my list, and I was going.

In my 20s, I’d spent most of my vacations visiting family and going to other people’s weddings. At 31, I needed an itinerary that was entirely my own. All I wanted to do was traverse Santorini’s dramatic calderas, relax on the beach and take in some extraordinary sunsets. As far as companionship, Henry Miller’s account of his travels in prewar Greece would do just fine.

But my second day on the island, I stumbled upon a bookstore run by a gaggle of Americans and Brits, and promptly changed my mind about that no-romance pledge. Bounding down the stairs into a subterranean shop, with books stuffed in every nook and cranny as if they were messages left in the crevices of the Western Wall, I locked eyes with a bearded man at the cash register. I smiled at him but mostly to myself. Oh, it’s on, I thought. I didn’t know if he was single, but I knew he looked like my type.

After dinner, I returned to the bookstore’s patio to watch the sunset with a bottle of wine. While sharing it with that bearded cashier, he asked if I’d planned this vacation with someone else, as if I’d been tragically marooned with a honeymoon suite all to myself.

“No, I planned to come here alone,” I said, noting that it had been a rough couple of years, romantically. A lot of promising starts, but nothing lasting. The least I could do was take myself on a getaway, never mind that I was surrounded by lovers and families.

Over the next few days, I tagged along with him and the rest of the bookstore crew. I joined them for a twilight swim and a home-cooked meal on a neighboring island one night, and that bearded cashier invited me out for a one-on-one dinner the next. He was, in fact, single, and we were hitting it off. Back in my real life in the District, the men I usually dated ranged from boring lawyers to interesting-yet-flailing creatives. There was no one who’d done something as sexy and risky as opening a bookstore in a foreign country years before a financial crisis.

During our date, we talked more about our lives: Mine in Washington, which I often found lacking in the love department, especially as 20-somethings moved in and out of town so often; rarely did I meet someone looking for something real right when I was. And he talked about how lonely it could get, living in a place where everyone else was perpetually on holiday. He proceeded to fantasize about what a relationship between us might be like, joking about reserving a ticket to Dulles International Airport and all that might entail. Clearly this was a man who made his living selling fiction, yet I took in every word. And why not? What is a vacation if not a break from reality?

Every good trip, no matter the traveler’s relationship status, entails some kind of romance. Not necessarily in a person, but in the question: What would life be like if we ditched our life back home and stayed? Here was someone who’d done just that, and I found it incredibly intriguing. Like me, he was surrounded by honeymooners — not for a week, but all year round. Suddenly my own solo trip here made more sense.

I also realized that dating on vacation, while seemingly pointless, was actually incredibly freeing. In the District, my dates often felt forced and rote — as if we were auditioning one another for a life together. Now here I was, enjoying myself with someone I’d stumbled upon and connected with, rather than selected from a crowd of online-dating profiles. That serendipity, plus the knowledge that a vacation fling wouldn’t go anywhere lasting, resulted in that rare date where the pressure was off and the romance was on.

Later that night, after a climb through an old castle and more carousing with customers at the bookstore, he told me to hang on to our time together, saying: “When you’re back in your real life, whenever you’re sad, just know that I’m a little bit in love with you.”

I didn’t say it back, but I was, too.

When we said goodbye the next morning, he told me to write to him and come find him someday. A few weeks later, I did send him a handwritten note … and never heard back.

Nonetheless, our fling seemed to hold me back in my real life. I’d think: “What, you don’t own a bookstore on a Greek Island? How ordinary.”

Eventually, I did move on and let the memories just be. Three years later, when a mutual friend was visiting Santorini, bookstore guy and I hopped on FaceTime together. His fantasies about our relationship were alive as ever.

This time, though, I told him to stop with the storytelling.

Now, whenever I’m worn out or underwhelmed by the D.C. dating scene, instead of thinking of him, I occasionally think back at that trip as a symbol of romantic possibility: At any moment, my luck might change. There really are a world of options out there.